monosaccharide

monosaccharide

[mon-uh-sak-uh-rahyd, -er-id]
monosaccharide: see carbohydrate.

Any of the simple sugars that serve as building blocks for carbohydrates. They are classified based on their backbone of carbon (C) atoms: Trioses have three carbon atoms, tetroses four, pentoses five, hexoses six, and heptoses seven. The carbon atoms are bonded to hydrogen atoms (singlehorzbondH), hydroxyl groups (singlehorzbondOH; see functional group), and carbonyl groups (singlehorzbondCdoublehorzbondO), whose combinations, order, and configurations allow a large number of stereoisomers (see isomer) to exist. Pentoses include xylose, found in woody materials; arabinose, found in gums from conifers; ribose, a component of RNA and several vitamins; and deoxyribose, a component of DNA. Important hexoses include glucose, galactose, and fructose. Monosaccharides combine with each other and other groups to form a variety of disaccharides, polysaccharides, and other carbohydrates.

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Monosaccharides (from Greek μόνος: single, sacchar: sugar) are the most basic unit of carbohydrates. They consist of one sugar and are usually colorless, water-soluble, crystalline solids. Some monosaccharides have a sweet taste. Examples of monosaccharides include glucose (dextrose), fructose, galactose, xylose and ribose. Monosaccharides are the building blocks of disaccharides such as sucrose (common sugar) and polysaccharides (such as cellulose and starch). Further, each carbon atom that supports a hydroxyl group (except for the first and last) is chiral, giving rise to a number of isomeric forms all with the same chemical formula. For instance, galactose and glucose are both aldohexoses, but have different chemical and physical properties.

Structure

With few exceptions (e.g., deoxyribose), monosaccharides have the chemical formula Cx(H2O)y with the chemical structure H(CHOH)nC=O(CHOH)mH. If n or m is zero, it is an aldehyde and is termed an aldose, otherwise it is a ketone and is termed a ketose. Monosaccharides contain either a ketone or aldehyde functional group, and hydroxyl groups on most or all of the non-carbonyl carbon atoms.

Cyclic structure

Most monosaccharides form cyclic structures, which predominate in aqueous solution, by forming hemiacetals or hemiketals (depending on whether they are aldoses or ketoses) between an alcohol and the carbonyl group of the same sugar. Glucose, for example, readily forms a hemiacetal linkage between its carbon-1 and the hydroxyl group of its carbon-5. Since such a reaction introduces an additional stereogenic center, two anomers are formed (α-isomer and β-isomer) from each distinct straight-chain monosaccharide. The interconversion between these two forms is called mutarotation.

A common way of representing the cyclic structure of monosaccharides is the Haworth projection. In Haworth projection, the α-isomer has the OH- of the anomeric carbon under the ring structure, and the β-isomer, has the OH- of the anomeric carbon on top of the ring structure. In chair conformation, the α-isomer has the OH- of the anomeric carbon in an axial position, whereas the β-isomer has the OH- of the anomeric carbon in equatorial position.

Monosaccharide nomenclature

Monosaccharides are classified by the number of carbon atoms they contain:

Monosaccharides are classified the type of carbonyl group they contain:

Isomerism

The total number of''' possible stereoisomers of one compound (n) is dependent on the number of stereogenic centers (c) in the molecule. The upper limit for the number of possible stereoisomers is n = 2c. The only carbohydrate without an isomer is dihydroxyacetone or DHA.

Monosaccharides are classified according to their molecular configuration at the chiral carbon furthest removed from the aldehyde or ketone group. The chirality at this carbon is compared to the chirality of carbon 2 on glyceraldehyde. If it is equivalent to D-glyceraldehyde's C2, the sugar is D; if it is equivalent to L-glyceraldehyde's C2, the sugar is L. Due to the chirality of the sugar molecules, an aqueous solution of a D or L saccharides will rotate light. D-glyceraldehyde causes polarized light to rotate clockwise (dextrorotary); L-glyceraldehyde causes polarized light to rotate counterclockwise (levorotary). Unlike glyceraldehyde, D/L designation on more complex sugars is not associated with their direction of light rotation. Since more complex sugars contain multiple chiral carbons, the direction of light rotation cannot be predicted by the chirality of the carbon that defines D/L nomenclature.

All these classifications can be combined, resulting in names like D-aldohexose or ketotriose.

List of monosaccharides

This is a list of some common monosaccharides, not all are found in nature—some have been synthesized:

Reactions

  1. Formation of acetals.
  2. Formation of hemiacetals and hemiketals.
  3. Formation of ketals.

See also

References

External links

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